Cu(I)/DTBM-BIPHEP-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides with cis-trifluorocrotonate for asymmetric construction of trifluoromethylated pyrrolidines

Tetrahedron Letters

Volumn 53, Issue 28, 2012, Pages 3650-3653

  Li, Qing Hua ^a   Xue, Zhi Yong ^a   Tao, Hai Yan ^a   Wang, Chun Jiang ^a,b  

^a WUHAN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

1,3 Dipolar cycloaddition; Asymmetric catalysis; Pyrrolidine; Stereoselectivity; Trifluoromethyl group

Indexed keywords

4,4,4 TRIFLUOROCROTONATE; COPPER; CROTONIC ACID DERIVATIVE; METHYL GROUP; PYRROLIDINE DERIVATIVE; TRIFLUOROMETHYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; NONHUMAN; STAPHYLOCOCCUS AUREUS;

EID: 84861965132     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.021     Document Type: Article

References (48)

1. L.M. Harwood, and R.J. Vickers A. Padwa, W. Pearson, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products 2002 Wiley & Sons New York
2. J.P. Michael Nat. Prod. Rep. 25 2008 139
3. For recent reviews about 1,3-dipolar cycloaddition reactions of azomethine ylides, see: B. Engels, and M. Christl Angew. Chem., Int. Ed. 48 2009 7968
4. L.M. Stanley, and M.P. Sibi Chem. Rev. 108 2008 2887
5. M. Alvarez-Corral, M. Munoz-Dorado, and I. Rodrguez-Garca Chem. Rev. 108 2008 3174
6. M. Naodovic, and H. Yamamoto Chem. Rev. 108 2008 3132
7. M. Bonin, A. Chauveau, and L. Micouin Synlett 2006 2349
8. C. Nájera, and J.M. Sansano Angew. Chem., Int. Ed. 44 2005 6272
9. V. Nair, and T.D. Suja Tetrahedron 63 2007 12247
10. J. Adrio, and J.C. Carretero Chem. Commun. 47 2011 6784
11. S.L. Schreiber Science 2000 1964 287
12. For the very recent examples, see: H.Y. Kim, J.-Y. Li, S. Kim, and K. Oh J. Am. Chem. Soc. 133 2011 20750
13. L. He, X.-H. Chen, D.-N. Wang, S.-W. Luo, W.-Q. Zhang, J. Yu, L. Ren, and L.-Z. Gong J. Am. Chem. Soc. 133 2011 13504
14. J.-F. Bai, L.-L. Wang, L. Peng, Y.-L. Guo, J.-N. Ming, F.-Y. Wang, X.-Y. Xu, and L.-X. Wang Eur. J. Org. Chem. 2011 4472
15. M.-N. Cheng, H. Wang, and L.-Z. Gong Org. Lett. 13 2011 2418
16. T.-L. Liu, Z.-L. He, H.-Y. Tao, Y.-P. Cai, and C.-J. Wang Chem. Commun. 47 2011 2616
17. T.-L. Liu, Z.-L. He, and C.-J. Wang Chem. Commun. 47 2011 9600
18. T.-L. Liu, Z.-Y. Xue, H.-Y. Tao, and C.-J. Wang Org. Biomol. Chem. 2011 1980 9
19. R. Robles-Machin, I. Alonso, J. Adrio, and J.C. Carretero Chem.-Eur. J. 17 2011 13118
20. F. Shi, S.-W. Luo, Z.-L. Tao, L. He, J. Yu, S.-J. Tu, and L.-Z. Gong Org. Lett. 13 2011 4680
21. H.-L. Teng, H. Huang, H.-Y. Tao, and C.-J. Wang Chem. Commun. 47 2011 5494
22. H. Wu, B. Wang, H. Liu, and L. Wang Tetrahedron 67 2011 1210
23. Z.-Y. Xue, X. Fang, and C.-J. Wang Org. Biomol. Chem. 9 2011 3622
24. I. Oura, K. Shimizu, K. Ogata, and S.-I. Fukuzawa Org. Lett. 12 2010 1752
25. R. Robles-Machín, I. Alonso, J. Adrio, and J.C. Carretero Chem.-Eur. J. 16 2010 5286
26. Z.-Y. Xue, T.-L. Liu, Z. Lu, H. Huang, H.-Y. Tao, and C.-J. Wang Chem. Commun. 46 2010 1727
27. J. Yu, W.-J. Chen, and L.-Z. Gong Org. Lett. 12 2010 4050
28. T. Arai, A. Mishiro, N. Yokoyama, K. Suzuli, and H. Sato J. Am. Chem. Soc. 132 2010 5338
29. T. Arai, N. Yokoyama, A. Mishiro, and H. Sato Angew. Chem., Int. Ed. 49 2010 7895
30. C. Zhang, S.-B. Yu, X.-P. Hu, D.-Y. Wang, and Z. Zheng Org. Lett. 12 2010 5542
31. I. Ojima Fluorine in Medicinal Chemistry and Chemical Biology 2009 Wiley-Blackwell New York
32. J.-P. Bégu, and D. Bonnet-Delpon Bioorganic and Medicinal Chemistry of Fluorine 2008 John Wiley & Sons, Inc. New York
33. V.P. Kukhar, and V.A. Soloshonok Fluorine Containing Amino Acids-Synthesis and Properties 1995 Wiley Chichester
34. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320
35. R. Smits, C.D. Cadicamo, K. Burger, and B. Koksch Chem. Soc. Rev. 37 2008 1727
36. J. Nie, H.-C. Guo, D. Cahard, and J.-A. Ma Chem. Rev. 111 2010 455
37. H. Fukui, T. Shibata, T. Naito, J. Nakano, T. Maejima, H. Senda, W. Iwatani, Y. Tatsumi, M. Suda, and T. Arika Bioorg. Med. Chem. Lett. 8 1998 2833
38. D. Bonnet-Delpon, A. Chennoufi, and M.H. Rock Bull. Soc. Chim. Fr. 132 1995 402
39. Q.-H. Li, M.-C. Tong, J. Li, H.-Y. Tao, and C.-J. Wang Chem. Commun. 47 2011 11110
40. Y. Yamashita, X.-X. Guo, R. Takashita, and S. Kobayashi J. Am. Chem. Soc. 132 2010 3262
41. Y. Yamashita, I. Takaki, and S. Kobayashi Angew. Chem., Int. Ed. 50 2011 4893
42. A. López-Pérez, J. Adrio, and J.C. Carretero J. Am. Chem. Soc. 130 2008 10084
43. S.-I. Fukuzawa, and H. Oki Org. Lett. 10 2008 1747
44. A. López-Pérez, J. Adrio, and J.C. Carretero Angew. Chem., Int. Ed. 48 2009 340
45. R. Robles-Machin, M. González-Esguevillas, J. Adrio, and J.C. Carretero J. Org. Chem. 75 2010 233
46. X.-X. Yan, Q. Peng, Y. Zhang, K. Zhang, W. Hong, X.-L. Hou, and Y.-D. Wu Angew. Chem., Int. Ed. 45 2006 1979
47. W. Gao, X. Zhang, and M. Raghunath Org. Lett. 7 2005 4241
48. Y. Oderaotoshi, W. Cheng, S. Fujitomi, Y. Kasano, S. Minakata, and M. Komatsu Org. Lett. 5 2003 5043